Asymmetrical mono-carbonyl ferrocenylidene curcumin and their dihydropyrazole derivatives: Which possesses the highest activity to protect DNA or scavenge radical?

Li, Pei-Ze; Liu, Zai‐Qun

doi:10.1007/s00044-014-0924-1

Cited by 9 publications

(3 citation statements)

References 30 publications

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“…As depicted in Figure 5, the n value of chalcone 43 (3.7) is increased to 17.7 for 50, demonstrating that antioxidative effect can be improved markedly after a linear chalcone performs a cyclization with phenylhydrazine to afford 4,5-dihydro-1H-pyrazole skeleton. [30] We next conduct the influence of the position of ferrocene moiety (at 3-or 5position in the scaffold of dihydropyrazole) on antioxidative effect. Comparison of n value of 44 (0.0) with that of 47 (2.2) (see left column chart in Figure 5) indicates that the combination of 3-ferrocenyl with 5-phenyl as in 47 other than the converse sequence as in 44 is able to generate antioxidative property by ferrocene moiety rather than by the phenolic hydroxyl group, and this antioxidative property is attributable to the aromatization of dihydropyrazole scaffold because the n value decreases to 0 after dihydropyrazole in 47 is aromatized to form pyrazole.…”

Section: Attaching To Aromatic Ringsmentioning

confidence: 99%

Enhancing Antioxidant Effect against Peroxyl Radical‐Induced Oxidation of DNA: Linking with Ferrocene Moiety!

Liu

2019

The Chemical Record

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As a major member in the family of reactive oxygen species, peroxyl radical is able to abstract hydrogen atom from 4‐position of ribose, leading to the collapse of DNA strand. Thus, inhibiting oxidative stress with exogenous antioxidants acts as a promising strategy to protect the integrity of DNA structure and is thereby suggested to be a pathway against developments of related diseases. Ferrocene as an organometallic scaffold is widely applied in the design of organometallic drugs, and redox of Fe(II)/Fe(III) in ferrocene offers advantage for providing electron to radicals. Presented herein are our ongoing studies on ferrocene‐appended antioxidants, including McMurry reaction applied to construct ferrocifen; Aldol condensation used to prepare ferrocenyl curcumin; Povarov reaction employed to prepare ferrocenyl quinoline; Biginelli reaction used to construct ferrocenyl dihydropyrimidine; Groebke reaction used to synthesize ferrocenyl imidazo[1,2‐a]pyridine; and Passerini three‐component reaction as well as Ugi four‐component reaction applied to synthesize α‐acyloxycarboxamide and bisamide, respectively. It is found that ferrocene moiety is able to enhance antioxidative effect of the aforementioned scaffolds even without the aid of phenolic hydroxyl group. The role of ferrocene in enhancing antioxidative effect can be attributable to trapping radicals, decreasing oxidative potential, and increasing the affinity toward DNA strand. Therefore, ferrocene is worthy to be taken into consideration in the design of drugs in relation to DNA oxidation.

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Section: Attaching To Aromatic Ringsmentioning

confidence: 99%

Enhancing Antioxidant Effect against Peroxyl Radical‐Induced Oxidation of DNA: Linking with Ferrocene Moiety!

Liu

2019

The Chemical Record

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“…via aldol and Knoevenagel condensation. It was obtained in low yield, and it exhibited good antioxidant activity [28] . Lange et al .…”

Section: Introductionmentioning

confidence: 99%

Hybrid Compounds Containing a Ferrocene Scaffold as Potential Antimalarials

2021

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Malaria is an infectious disease, and it remains a serious health problem globally. The drugs developed for its treatment suffer from several shortcomings such as low water solubility, poor bioavailability, drug toxicity, and resistance. Molecular hybridization of different bioactive agents is a promising approach for developing hybrid compounds with improved therapeutic effects. Ferrocene, an organometallic, has been hybridized with several pharmacophores resulting in compounds with potent biological activities. In this research, a modified ferrocene scaffold was hybridized with selected pharmacophores. The synthesized compounds were characterized by Fourier‐Transform Infrared Spectroscopy (FTIR), Nuclear Magnetic Resonance Spectroscopy (NMR), and Liquid Chromatography‐Mass Spectroscopy. The hybrid compounds were obtained in good yields (53–76 %). In vitro evaluation against NF54 (drug‐sensitive) strain of Plasmodium falciparum parasites revealed the compounds, 16 and 19 (hybrids containing artesunate scaffold), together with 18 and 21 (hybrids containing oleanolic acid scaffold), as promising antimalarial agents. These compounds displayed IC50 values of 116.73±3.18, 56.33±15.20, 78.22±21.05, and 58.22±15.20 nM, respectively. These findings revealed the potency of ferrocene as a precursor for the development of promising antimalarials.

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“…These properties have led to the development of a vast number of ferrocene derivatives and their applications in a wide range of research areas such as catalytic organic synthesis, biological and medicinal chemistry, agrochemicals and materials science. [5][6][7][8][9][10][11][12][13][14][15] Consequently, there is a continuous endeavour to design and synthesize ferrocene containing new molecules, which will have potential utility as functional materials or catalysts in organic synthetic reactions. Recently, we have reported a dipalladium(II) complex with a ferrocene containing diphosphine ligand 16 and its application as catalyst in C-C cross coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

N-(acyl)- $$\textit{N}^\prime $$ N ′ -(ferrocenylidene)hydrazines and their nickel(II) complexes: Syntheses, structures and physical properties

Babu

Pal

2017

J Chem Sci

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The Schiff bases N-(acyl)-N-(ferrocenylidene)hydrazines (HFcah (1) and HFcbh (2), where acyl = acetyl in 1 and benzoyl in 2 and H represents the dissociable amide proton) were synthesized in high yields (74 and 81%) by condensation reactions of equimolar amounts of ferrocene-carboxaldehyde and the corresponding acylhydrazines in presence of acetic acid in refluxing methanol. Reactions of Ni(OAc) 2 •4H 2 O, the Schiff bases (1 and 2) and NaOAc • 3H 2 O in 1:2:4 mole ratio in refluxing methanol afforded the diamagnetic iron(II)-nickel(II)iron(II) species [Ni(Fcah) 2 ] (3) and [Ni(Fcbh) 2 ] (4) in 60 and 68% yields, respectively. Both Schiff bases and the two trinuclear complexes were characterized by elemental (CHN) analysis, mass spectrometric, various spectroscopic (IR, UV-Vis and 1 H NMR) and cyclic voltammetric measurements. Molecular structures of 2, 3 and 4 were determined by single crystal X-ray diffraction studies. The cyclopentadienide rings in the ferrocene moieties are essentially in eclipsed conformation in all three structures. Deprotonated Schiff base ligands in each complex (Fcah − in 3 and Fcbh − in 4) act as five-membered chelate ring forming azomethine-N and amidate-O donors and assemble a square-planar trans-N 2 O 2 coordination environment around the nickel centre. The redox active 1-4 exhibit an iron centred redox couple in the potential range 0.23-0.50 V (vs. Ag/AgCl).

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Asymmetrical mono-carbonyl ferrocenylidene curcumin and their dihydropyrazole derivatives: Which possesses the highest activity to protect DNA or scavenge radical?

Cited by 9 publications

References 30 publications

Enhancing Antioxidant Effect against Peroxyl Radical‐Induced Oxidation of DNA: Linking with Ferrocene Moiety!

Enhancing Antioxidant Effect against Peroxyl Radical‐Induced Oxidation of DNA: Linking with Ferrocene Moiety!

Hybrid Compounds Containing a Ferrocene Scaffold as Potential Antimalarials

N-(acyl)- $$\textit{N}^\prime $$ N ′ -(ferrocenylidene)hydrazines and their nickel(II) complexes: Syntheses, structures and physical properties

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